Oakland Vacations from $354
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Your Oakland Vacation
From its cycling to its walking, there's tons to love about Oakland. Book a customized Oakland vacation package and get ready to fall for the delights of this neighborhood. When it's time to head out and explore, you'll find lots of big-name attractions nearby including Acrisure Stadium, University of Pittsburgh and PNC Park. Tick off one, two or all during your trip to Oakland. No matter your travel plans or budget, booking the ultimate Oakland vacation is simple with Expedia.
The Latest Oakland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Indigo Pittsburgh East Liberty by IHG
East Liberty
per person
Aug 14 - Aug 17
found 7 hours ago
Roundtrip flight included
Los Angeles (LAX) to Pittsburgh (PIT)
8.2/10 Very Good! (1,010 reviews)
Front desk staffs were excellent and quick check in and check out. Room was good size and very clean.
Breakfast was not that great. Parking is available per Expedia portal so I misunderstood it will be a free self parking but valet parking only. Very expensive. OK, to stay if you dont want to pay too much for one night.
Reviewed on Jun 28, 2025
Seven Springs Resort Properties
Save 100% on your flight
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Pittsburgh (PIT)
8/10 Very Good! (12 reviews)
The condo was perfect for our family. 3 bedrooms, 3 bathrooms and a kitchen with plenty of pots/pans/utensils to cook your own meals. Its a great place to get away with the family in nature, play board games and just spend time together.
Reviewed on Jun 28, 2025
Omni William Penn Hotel
Downtown Pittsburgh
per person
Aug 14 - Aug 17
found 7 hours ago
Roundtrip flight included
Los Angeles (LAX) to Pittsburgh (PIT)
9/10 Wonderful! (1,503 reviews)
Madeline- our waitress was excellent!!, Friendly and professional, took quick care of us on a busy night, always checked in to see how we were. She truly made us feel at home, excellent staff!!
The room was spacious and clean.The bed was so comfortable, we didnt want to leave. Would definitely come here again
Reviewed on Jul 1, 2025
Where to stay in Oakland
Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Downtown Pittsburgh
2 out of top 10 points of interest in this area
4.5/5(2,251 area reviews)
Discover the urban downtown center, home to historic sites like Point State Park and the Cultural District. Enjoy diverse shopping options and easy access to public transportation, including the "T" light rail and bus networks.
Oakland Hotel Deals
Courtyard by Marriott Pittsburgh University Center
100 Lytton Avenue, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $136 total per night from Jul 3 to Jul 4
$136 total
Jul 3 - Jul 4
Total includes taxes and fees
8.8/10 Excellent! (356 reviews)
"Hotel was OK for our purposes. Restaurant/Dining area not up to much and expensive. Most staff were quite helpful."
Reviewed on Jun 26, 2025
Hampton Inn Pittsburgh University/Medical Center
3315 Hamlet Street, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $115 total per night from Jul 13 to Jul 14
$115 total
Jul 13 - Jul 14
Total includes taxes and fees
8/10 Very Good! (1,038 reviews)
"Comfy beds"
Reviewed on Jun 29, 2025
Hotel Indigo Pittsburgh University-Oakland by IHG
329 Technology Drive, Pittsburgh, PA
Fully refundable
$119 nightly
The price is $136 total per night from Jul 27 to Jul 28
$136 total
Jul 27 - Jul 28
Total includes taxes and fees
8.6/10 Excellent! (1,005 reviews)
"Hotel Indigo has a cool modern industrial look. Is high end for average costs"
Reviewed on Jun 26, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Discover the most popular places to visit in Oakland
University of Pittsburgh
4.5/5(843 reviews)
Enjoy the collegiate vibe around University of Pittsburgh, a top college in Pittsburgh. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.
Carnegie Museum of Natural History
4.5/5(48 reviews)
From rare jaguars to geological marvels and ancient fossils, you’ll find it all at this Pittsburgh institution, one of the country’s largest natural history museums.
Carnegie Museum of Art
5/5(4 reviews)
If you like your art with a modern twist, you’re in for a treat at this exceptional museum, which also features impressive furniture and architecture galleries.
Things to do
Private City Kickstart Tour: Tokyo
$134
per adult
100% of travellers recommend
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
$13
per adult
Pittsburgh: Beauty of the Burgh Bike Tour
$59
per adult
100% of travellers recommend
Explore a world of travel with Expedia
Explore a world of travel with Expedia
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- University of Pittsburgh
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- Petersen Events Center
- Cathedral of Learning
- Soldiers and Sailors Memorial Hall and Museum
- Carnegie Museum of Natural History
- Heinz Memorial Chapel
- Carnegie Museum of Art
- Phipps Conservatory
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- Carnegie Mellon University
- Hunt Institute for Botanical Documentation
- Pittsburgh Opera
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- Clemente Museum
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- Contemporary Craft
- Market Square
- Visit Pittsburgh
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- PPG Paints Arena
- Temple Sinai
- Senator John Heinz Regional History Centre
- Duquesne University
- Walnut Street
- Western Pennsylvania Sports Museum
- Visit Shadyside
- Roberto Clemente Bridge
- Chatham University
- Visit Bloomfield
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.